Florpyrauxifen-benzyl (Ref: XDE-848 BE)

Florpyrauxifen-benzyl (Ref: XDE-848 BE)	Last updated: 23/01/2021
(Also known as: XR-848)

GENERAL INFORMATION

Description

A new post-emergence herbicide with various applications including as a rice weed herbicide particularly in Australia

Example pests controlled

Grass weeds including barnyard grass; Sedges; Broad-leaf weeds including water plantain, starfruit, arrowhead, jerry jerry and dirty Dora

Example applications

Rice

Efficacy & activity

Shown to be highly effective in research studies

Availability status

Current

Introduction & key dates

2016

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Italy/Austria

Date EC 1107/2009 inclusion expires

24/07/2029

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

Also used in

Chemical structure

Isomerism

Chemical formula

C₂₀H₁₄Cl₂F₂N₂O₃

Canonical SMILES

COC1=C(C=CC(=C1F)C2=NC(=C(C(=C2F)N)Cl)C(=O)OCC3=CC=CC=C3)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

WNZCDFOXYNRBRB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C20H14Cl2F2N2O3/c1-28-19-12(21)8-7-11(14(19)23)17-15(24)16(25)13(22)18(26-17)20(27)29-9-10-5-3-2-4-6-10/h2-8H,9H2,1H3,(H2,25,26)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Pyridine

Minimum active substance purity

920 g kg⁻¹

Known relevant impurities

EU dossier: toluene < 3g kg⁻¹

Substance origin

Synthetic

Mode of action

CAS RN

1390661-72-9

EC number

CIPAC number

US EPA chemical code

PubChem CID

70495450

Molecular mass

439.25

PIN (Preferred Identification Name)

benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate

IUPAC name

benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate

CAS name

phenylmethyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Off-white to beige coloured solid with a mild odour

Related substances & organisms

florpyrauxifen

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Rinskor
Lorant

Example products using this active

Formulation and application details

Usually supplied as an emulsifiable concentrate for dilution and use in broadcast sprayers.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.011

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

13000

Methanol

210000

Acetone

14000

Xylene

120000

Ethyl acetate

Melting point (°C)

137.1

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

286.8

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

2.88 X 10⁰⁵

Calculated

Log P

5.46

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.2 X 10^-02

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

0.94

Moderately volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradeable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

150

Persistent

DT₅₀ (lab at 20 °C)

150.5

Persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

304.5

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

14.7

mean for flooded paddy soil system

Note

EU 2017 dossier lab studies DT₅₀ range 8.9-348 days, DT₉₀ range 30-7914 days; Flooded paddy field DT₅₀ range 8-10 days, DT₉₀ range 34-104 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.07

summer

Fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

111

Persistent

Note

pH and temperature sensitive

Water-sediment DT₅₀ (days)

4.9

Fast

Water phase only DT₅₀ (days)

3.3

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

804.5

Non-mobile

K_oc

32308

Notes and range

EU 2017 dossier K_d range 272-1377 mL g⁻¹, K_oc range 23028-47763 mL g⁻¹, Soils=5

Freundlich

K_f

634.8

Non-mobile

K_foc

22325

¹/_n

0.95

Notes and range

EU 2017 dossier, K_f range 130-1474 mL g⁻¹, K_foc range 15305-33500 mL g⁻¹, ¹/_n range 0.9-1.01, Soils=5

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.76

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

florpyrauxifen (Ref: X11438848)

Soil

0.62

Major fraction; Relevant

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxyphenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X11966341)

Soil

0.08

Minor fraction; Relevant

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxy-6-nitrophenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X12483137)

Soil

0.11

Major fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-hydroxyphenyl)-5-fluoropyridine-2-carboxylate (Ref: X12300837)

Soil, Water

benzyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (Ref: X12431091)

Plant

4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid (Ref: X12393505)

Water; Animal

4-amino-6-(4-chloro-2-fluoro-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-fluoropicolinic acid (Ref: X12131932)

Water; Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

326

Threshold for concern

CT₅₀ (days)

1.3

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

A5 Rat 5000

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.049

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 0.0626

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.0378

Daphnia magna

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.0785

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

> 0.0461

Lemna gibba

Moderate

Non-target plants

2.3

Carrot
Seedling emergence, ER₅₀
as g ha⁻¹

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 0.0337

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 105.4

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

67.5

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

972

=
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

1342

=
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose; 017-17 mg kg⁻¹ soil 28 days

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

A5 Rat 5000

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.23

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

3.00

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.5

Rat SF=2000

Dermal penetration studies (%)

0.45-11.4

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks identified

Occupational

No unacceptable risks identified

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

No information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317
Environment: H410

EC Risk Classification

EC Safety Classification

WHO Classification

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

florpyrauxifen-benzyl

French

florpyrauxifene-benzyle

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	23/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242